Xia Ai-Bao, Zhang Xiao-Long, Tang Cheng-Ke, Feng Kai-Xiang, Du Xiao-Hua, Xu Dan-Qian
Catalytic Hydrogenation Research Centre, State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou, 310014, China.
Org Biomol Chem. 2017 Jul 21;15(27):5709-5718. doi: 10.1039/c7ob00986k. Epub 2017 Jun 26.
An asymmetric formal one-pot reaction of 4-hydroxycoumarins with unsaturated pyrazolones has been developed by merging a chiral bifunctional organocatalyst with molecular iodine, which furnished a series of optically active spiro[dihydrofurocoumarin/pyrazolone] heterocycles with spiro quaternary stereogenic centers in moderate to excellent yields (up to 99%) with excellent diastereoselectivities (up to >99 : 1 dr) and good to excellent enantioselectivities (up to 99% ee). The application in the gram-scale synthesis of chiral spiro[dihydrofurocoumarin/pyrazolone] compounds was also successfully realized.
通过将手性双功能有机催化剂与分子碘相结合，开发了一种4-羟基香豆素与不饱和吡唑啉酮的不对称形式一锅反应，该反应以中等至优异的产率（高达99%）、优异的非对映选择性（高达>99:1 dr）和良好至优异的对映选择性（高达99% ee）提供了一系列具有螺环季立体中心的光学活性螺环[二氢呋喃并香豆素/吡唑啉酮]杂环。在手性螺环[二氢呋喃并香豆素/吡唑啉酮]化合物的克级合成中的应用也成功实现。
